


Isn't She Pretty?

by arxivewriter



Category: Supernatural
Genre: Angst, Crossdressing, Dean is an asshole, M/M, Schmoop, Teenagers, and then he isn't, but you never see her again, high school age, there is an OC at the beginning
Language: English
Status: Completed
Published: 2013-08-16
Updated: 2013-08-16
Packaged: 2017-12-23 17:40:51
Rating: Not Rated
Warnings: Underage
Chapters: 1
Words: 6,522
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/929279
Author URL: https://archiveofourown.org/users/arxivewriter/pseuds/arxivewriter
Summary: <blockquote class="userstuff">
              <p>Dean stopped short, entering the hotel room. Sam, Sammy, his little brother, was standing at the microwave, heating up a burrito and dancing to his portable CD player in a knee-length blue skirt, white blouse, and fucking flip flops. </p><p>(In which Sam likes skirts and Dean and Dean is a dick and then isn't.)</p>
            </blockquote>





	Isn't She Pretty?

**Author's Note:**

> Okay so this piece of shit was what I wrote for the anonymous kink meme (Underage) prompts. Unbeta'ed. All mistakes are mine, nothing else is except the awful plot.

It all started when Sam was twelve years old. His dad had decided on Dean’s 16th birthday that he was properly prepared to help with a hunt or two… and that Sam would be fine on his own for one night. Sam was left with uncle Bobby’s number, some preheated food for dinner, and movies to keep himself busy.  
He watched them pull out of the driveway and waved from the window until he was sure they were gone and not coming back. Then he raced to the phone and pulled out the number he’d gotten from the girl he’d met in class earlier that week. Her name was Sasha, she was completely crazy, and apparently she wanted to hang out.  
Maybe when Dean got home he’d finally have a story about a girl to tell him instead of the other way around.  
***  
She wanted to go shopping. Are you kidding? But Sam didn’t want to be stuck inside all day, and he really wanted to talk to someone, so he nodded and agreed his way through the conversation and hung up to get ready.  
“Fifteen minutes!” she’s said, assuring him that they were going to be fine and have lots of fun at the mall. He pulled on a fresh pair of cargo shorts and loose t shirt, looking at himself in the mirror before shrugging. He didn’t really care about his looks, but Dean always said impressing a girl really happened in the first five seconds.  
He also said fresh breath was a big thing, so Sam gargled with the mouthwash by the bathroom sink and sprayed some of his brother’s body spray… something caled ‘Fire and Ice’ that made him want to sneeze but apparently girls loved?  
Whatever.  
He grabbed a bit of the cash Dad had left him, made himself comfortable in front of the hotel, and smiled when a white minivan dove up. Sasha let him in and chattered all the way to the mall.  
***  
He was having fun, surprisingly. Sasha was friendly and, even if she had no idea what soccer was about, told interesting stories about her brothers and sister and the way they’d recently bought a Playstation and he could come over if he wants to play around. She was different than any of the Hunter kids he’d met on the road or at Aunt Ellen’s Roadhouse. She was certainly nicer than Jo, the girl two years his junior who pulled his hair and told him he was a pansy when he didn’t let her put a bunch of little braids in it or wrestle her.  
When they got to the mall the two of them split off from her older brother, who was looking for some new Girbaud jeans and Keds apparently. Sasha grinned and grabbed Sam’s hand, pulling him into some clothing store.  
He let himself be pulled over to the babydoll dress section and smiled as she immediately began looking them over and talking about how each of them were so cute, how could she even choose one. Sam’s eyes skimmed over the dresses and he found himself lingering over a blue dress with tan trim. It was nice looking, and on impulse he picked it up and held it out for her.  
“You should try this on.” He smiled and nodded and she looked it over seriously.  
“I don’t know, it’s not really my color.” She looked at it, then back to him, then to the dress again. A weird look crossed her face and Sam began to worry.  
“I know, why don’t you try it on? I’ll do this one!” She picked up a yellow dress of a different style and grinned, shoving his choice back into his chest.  
Sam had no idea how to react. He wanted to cringe away and laugh, tell her there’s no way, but… A little part of him liked the idea of wearing something soft and clingy; something Dad would never even let him touch.  
“Uh…” He stared at it instead, until Sasha took his arm again and pretty much dragged him into the girls’ hanging rooms.  
A woman working there looked them both over and might have commented, but Sasha meat her to it.  
“Come on Sammy, you’ve got to try on a dress, stop dressing like such a boy!” She giggled and Sam’s cheeks reddened. Sasha pushed him into a changing room and took the one next to him and kept talking even as Sam stared at the dress in his hands. Was he actually supposed to put it on? What was even happening?  
****  
“Sammy, I know you’re not doing it yet, but you gotta put it on or I won’t let you come out of the stall!” She said in a singsong voice and Sam cringed. From what he’d seen of her in school, she wasn’t kidding.  
He pulled his shirt off and dropped it on the bench, staring at himself in the full length mirror. Could he do this?  
The little part of him that had been nagging to do it since he laid eyes on the thing, the same part that used to make him ogle ladies’ magazines at the store (No Dean, I’m not looking at their boobs), finally told him that nothing would happen. What would he lose? A little self respect, probably, and a secret he’d eventually tell Dean and be teased about. But it wasn’t like he was going to ever do it again.  
He slipped his shorts off as well, taking the pretty piece of cloth in hand, unzipping it, and pulling it gently over his head. That was how you were supposed to do it, right?  
He got it on finally and reached under the armpit to zip it up.  
It was… New. Odd, looking at the fabric on his skin. It didn’t really look that bad, he thought. No, if anything he maybe, sort of, a little tiny bit, liked it.  
Sasha burst in right then and Sam went to cover himself immediately, but she just laughed and tugged on him again, pulling him out of the changing room and showing him off like a doll to the worker.  
“Isn’t she pretty?” She giggled again and Sam felt horrified. If anyone was going to know it would be a professional salesperson. But the woman just smiled and nodded.  
“Sweetie, you look great.” She patted Sam’s arm and he flinched then nodded. She didn’t… Didn’t he look like a man? Wasn’t he manly?  
He caught a glimpse of himself in one of the mirrors behind the woman. No, he was not. But he did look kind of cute, even he had to admit.  
Sasha grinned at him and turned to the woman. “I want them both! Can you just ring them up without us taking them off?”  
The woman did, letting Sasha chatter as she laid a credit card Sam knew wasn’t hers, and hoped she’d had permission to use.  
Sasha took Sam’s clothing without even stopping for breath and balled them up, stuffing them in her bag before wrinkling her nose. “Are you wearing boxers?”  
Sam turned even redder than before. “Does it matter?” He automatically went to cover his crotch and Sasha laughed again. “No, it doesn’t really matter. Come on, let’s go get Icees!” Sam felt ridiculous, but they stayed at the mall for close to two hours before Sasha’s bother collected them from the book store.  
“Aren’t you a boy?” He asked as soon as he saw them. Sam’s eyes went wide as they could and he froze, unsure what to do, but Sasha covered him.  
“You thought Samantha was a boy? Oh my gosh, Danny, you’re ridiculous!” She started laughing and Sam joined in awkwardly. So did Danny, obviously embarrassed, and that was the last it was mentioned.  
Sam went home that day, still in the dress, and nearly panicked when he realized he would have to get back into the hotel without his dad or Dean seeing. Luckily it looked like it was a little more than a milk run, so Sam slipped inside and decided to wait a few more minutes before he changed. Sasha had given him the dress, so there was no concern about what he did with it.  
He decided to do a couple chores in it and maybe watch a movie and by the time his self-imposed bedtime rolled around, he thought maybe he could make this happen… one more time.  
When Dean and Dad got home from the trip, if Sammy looked a little happier and brooded a little less, they didn’t comment. It felt like the start of something that Sammy could really enjoy. 

 

****  
It was the summer of 1995, a balmy Saturday in June, and Sam had the whole apartment to himself this time. Dean and Dad were out on a hunt that would take a couple days to complete, so Sammy saw no problem running down to the local thrift store and picking up a pale pink denim skirt and white ruffly blouse, trading his sandals for white flip flops at the dollar store. He’d learned that people commenting on his choice wasn’t something he could avoid, but he didn’t really mind so much. He’d never see any of the people again; who were they to ruin his day?  
Back at home he kicked off his flip flops and turned on the stereo, flipping to the local station where “Summer Time” by Shaggy was playing. He flopped on the bed and turned on the TV, since there was no homework or case work to do. Star Trek Voyager was on, and he smirked. Dean would be so pissed about missing it.  
Thoughts of Dean annoyed led to thoughts of Dean amused, to Dean in general and all of a sudden it was a parade of naked Deans in his head and Sam sighed. Again?  
He’d begun to see boys in the sexual light when he was thirteen, right about the time things started to get bad with Dad. It was just one more secret to hide. He couldn’t even bring himself to tell Dean that he didn’t see girls like he should; that instead of pretty bubblegum-pink lips and curvy figures he jerked off to the thought of strong arms holding him and stubble-rough kisses.  
The worst of it was that those strong arms and rugged caresses belonged to none other than Dean himself. Sam was fourteen and he tried to convince himself that it was just a phase, but he knew it wasn’t. Trying for girls had been a phase he’d outgrown last year, right after he asked a girl if he could try on her shoes and she sucker-punched him. Turns out not all girls were as understanding or enabling as Sasha had been. After that he kept to himself about his clothing and his attractions. He reached down and rolled the thick skirt up, rubbing at the front of his briefs (The closest he could get to panties without running the risk of his Dad finding them).  
Every new town warranted a trip to the closest thrift store as soon as Dean and Dad disappeared for a hunt. Every time it was a different style and he got to enjoy them for maybe a couple days before the Impala rumbled back into town and Sam stuffed the offending articles in a trash bag, tossing them in a trash bin or donation bin on the way out. So far no one had questioned him and he was in the clear, but sometimes things got hard.  
Like his dick, as right now.  
He closed his eyes and tugged at the outline of his member through the thin cloth, sighing and letting thoughts of Dean come to mind.  
Dean, looking at him in surprise that morphed into arousal as Sam showed him his skirt. Maybe Dean would run his hands down Sam’s sides until he could tug it and his underwear down, over his skinny hips, and let his cock bounce up and smack him in the tummy.  
Sam smiled at the thought and pulled his underwear down, tugging down his skirt after it to follow the fantasy. He pretended it was Dean’s hand, skimming over his balls to caress his shaft. Dean would tell him he looked beautiful, that he was a pretty boy, a good boy, the best. He would rub Sam for a few minutes, then put his fingers to Sam’s closed lips.  
“Suck, pretty boy.” He would say, and Sam moaned quietly as he pushed his own fingers into his mouth. Dean would press down on his tongue, tell him to wet his fingers because where they were going he’d need it.  
Sam shuddered at the thought of Dean’s voice rough and low in his ear, whispering for him to let go, take them out, time to relocate those digits. He did so with no hesitance, moaning as he circled his tight pucker and pushed his first finger in.  
****  
It burned, to be honest, and Sam vaguely wondered if he could find any petroleum jelly or, hell, lube. He hated to do it, but he opened his eyes and rubbed his cock one more time before pulling his skirt all the way off and heading over to Dean’s duffel. He was a red-blooded male, and him, so there was bound to be at least lotion for exactly this purpose.  
He dug around the bottom and paused as his fingers brushed over something smooth and flat. Dean had a book? Dean didn’t READ books. He found the lube and pulled it out, choosing to ignore the mystery object for now in favor of Dean’s imaginary voice calling him back to the bed, telling him to hurry, not make him wait.  
He rushed back to the bed and imagined Dean going for his dick with enthusiasm, but this time licking at it and sucking the head into his mouth. He imagined Dean’s muffled hums and felt pleasure begin to ball up in his stomach.  
“Yes, Dean, perfect… Just like that.” He let the words tumbled from his lips once the silence was broken; speaking a litany of praise and “please” and “so good” as he worked his cock faster, then popped open the lube with one hand and took a moment to rub some on his fingers.  
Sam’s ass opened up easier with the lube. He squirmed at the still-unfamiliar feeling of one finger and hoped someday Dean would be able to open him up without him whining like a little bitch.  
Or maybe Dean would like that. He added a second finger and gasped.  
Maybe Dean would command him, like Dad, but more intimate. Tell him what to do, where and how to move, physically move him if he was too slow.  
Maybe Dean would be rough.  
Sam groaned at the thought and shoved his fingers in as far as possible and all too quickly was shooting his load right there on the bed, up to his stomach and over his hand.  
He sat up after a few minutes in the afterglow and looked down at his dirty midsection. After a moment’s hesitation he grabbed his underpants and used them to wipe the cum off his belly, tossing them on the floor and standing to go to the bathroom.  
A sense of dissatisfaction and shame curled up from his belly and he sighed as he turned on the shower. Dean would never like him like that, no matter what he wore. He would never live out his fantasies. And he should be relieved about that, because his brother was healthy and sane and didn't want to fuck someone made from the same genes as him. But instead, it just hurt.  
That evening, the skirt went in the trash. He would stop then. Dean and Dad came home three miserable, pants-wearing days later and it was a whole month and a half before he gave in to the desire and picked out another.  
****

The time passed quickly. The family would move, settle down, Sam would help with research, Dean and Dad would head out for a hunt. “Be careful Sammy. Be good.” Two or three days to himself, a new skirt, sometimes a dress, sometimes matching shoes, masturbation, fantasies, chores. Sam even invested in a little black make-up kit. He learned the basics from magazines and TV, watching carefully through the mirror as professionals outlines eyes and cheeks and lips. He felt great, strong, confident in his dresses. Sometimes he even went out. As his fourteenth year passed and fifteenth followed, he finally felt happy. Hell, he was getting ready for college! When Dad was gone, everything was good. Even so, his little attraction to Dean didn’t let up like he thought it would. Instead he watched Dean grow from a dorky eighteen-year-old that hit on too many girls to a much stronger, more asserted twenty-year old… that still hit on too many girls. His lashes were long and Sam had begun cataloging exactly what it was that made him so attracted to Dean.  
He still couldn’t figure it out.  
But the make-up, the skirts, the fantasies, the happiness, all came to a head the summer of 1999, just after he turned 16. 

In honor of his 16th, Sam got a little something special on his trip to the store. The panties were blue with lace trim and matched his dark blue frilly skirt well. His top was white, button up silk and he loved the feeling of it rubbing against his bare chest. This hunt was bigger than the last, they should be gone for about four days, and Sam really liked the whole ensemble. Maybe he could keep the panties at least.  
He put them on as soon as he got home from the store and left his boy clothes on the floor. (He wore them just as much, more, than he did the skirts. They were great, and he liked well-enough just being that tallish high school kid, but… skirts.)  
He felt comfortable in the clothing, like they were made for him instead of basketball shorts or the awful shirts guys at school tucked into their jeans. He felt free and, as he had taken to doing, felt like dancing.  
Everything was fine for two whole days, but even Sam’s careful preparation and contingency plan couldn’t prepare him for the door opening quietly a whole day before planned, as Sam stood in front of the microwave and sang/danced along to Baby One More Time by Brittany Spears.  
****  
Dean stopped short, entering the hotel room. Sam, Sammy, his little brother, was standing at the microwave, heating up a burrito and dancing to his portable CD player in a knee-length blue skirt, white blouse, and fucking flip flops.  
What was going on? Why was Sammy wearing something so girly? They didn’t belong on him, what the fuck was he thinking?  
Before he could stop himself Dean was in action, crossing the floor and grabbing Sam’s wrist as he lifted one to spin. Sam’s eyes flew open and his face contorted to one of horror as Dean stared down at him.  
Dean didn’t understand. Was this a joke? What was Sammy even doing? He snatched Sam’s headphones off his head and down, squeezing the thick plastic band and feeling his chest rise and fall quickly.  
“Sammy.” That one word made Sam flinch like Dean hadn’t seen since, well, since last time Dad was home and angry. He instantly wanted to push Sam behind him and protect him from whatever was scaring Sam, but a moment too late he realized that it was himself. Instead Dean squashed the urge to shield and claim and looked down at Sam, trying to keep his face impassive or at least not scary. He couldn’t hurt Sammy, no matter what he was doing. Wearing.  
Even so.  
“What the fuck are you wearing, Sammy?” He asked, anger flaring up no matter how hard he tried to keep it at bay.  
Sam’s eyes were wet and panicky. He yanked his hand away from Dean and his CD player crashed to the floor, cracking. With both hands free Sam suddenly began tugging the… thing… off as quickly as possible. He was shaking, Dean noticed, and the zipper was stuck. To be honest Dean had no idea what to do, so he just watched as Sammy ripped the skirt’s seam in his haste to get out of the offending article. Next came the shirt, every button popped of and flying across the room. He dropped it to the ground and turned, completely nude now, sprinting into the bathroom at top speed.  
Something in Dean’s head snapped and he realized just what he’d done, said, to his Sammy.  
What? His Sammy? Just Sam.  
He shook his head and began to approach the bathroom, comfort Sammy, do anything at all, when he heard the sobbing.  
It was quiet but steady, and Sam didn’t normally cry like that. He was usually able to keep quiet, a steady trickle of tears that he’d perfected at eight when Dad tired of his sniffling sobs. But they were back, which meant Sam was in worse shape than he had been in a long time.  
Shame flooded over Dean as he realized what he’d actually done to his little brother. So he was wearing girl’s clothing! So? It was the freakin’ 90’s! If there was one time that should be accepted it was today! Even if-  
Even if Sammy was into… Could he call him on it? His time with Rhonda Hurley had taught him one thing: a guy liked what he liked.  
Dean breathed deeply and felt frustration tear at his inside. Shit! He’d freaked Sam out, who already acted like a spooked horse around Dad. What was he supposed to do now?  
He grabbed the lamp off the nightstand and hurled it at the wall. It was plugged in, but the cord swung it down and it shattered on the floor by Sammy’s bed.  
Sammy…  
Dean went over to the bathroom door and almost knocked, but hesitated. If he scared him, what could he do to fix it?  
“Sammy?” He asked quietly. “You okay?”  
There was no response, but the sobbing grew a little more muffled. Dean heard the sink turn on.  
“Sammy, it’s okay. I’m sorry. I was just… Let’s not talk about this again.” Dean nodded. Sam could do what he wanted, Dean didn’t even have to be involved. They could pretend he’d never come home early. Sam had had make-up on, the good kid, so that meant he’d been doing this for a while…  
Dean’s pupils dilated as he remembered what Sam had looked like, happily shimmying to some CD in an outfit Dean had only ever seen on the better looking girls at school. And wow, he made them look like average Jills. Sitting down on the bed he closed his eyes to appreciate the afterimage of his brother looking like a, well, a really classy chick.  
****  
He’d always had a nice face, Dean knew that from the time he had to start warning girls off him when Sam was in the 6th grade. (He was obviously too young and girls can’t really be trusted in middle school. Or high school. Not with Sammy.) Dean might have exercised a little free will in the shower a few times, thinking of Sammy helping him out the way a good boy should… But this, this was incredible.  
Dean couldn’t help it. He heaved himself up from the bed, walking up to the bathroom door, and knocked again.  
“Sammy, I wanna talk to you. I wanna…” He couldn’t just tell Sammy he wanted to see how he looked. That was stupid. Besides, his skirt… Dean turned and looked at the ripped pile of fabric on the floor. Beside it was Sam’s CD player.  
Guilt. Guilt and self-loathing warred in Dean’s chest. What had he really done? Like, really?  
He picked up the skirt and admired the color. Sammy had good taste. Underneath though, was something lighter. The pale blue slip of fabric made Dean’s eyes go wide.  
So it wasn’t just the outer clothing Sammy had tried out.  
Dean shook his head, trying to rid himself of the sudden images of Sam pulling on the soft lace panties, sliding the skirt up his smooth legs (Jesus Christ did he shave? Dean had to know)… He rubbed the panties between his fingers. They were nice, not cheap or scratchy. As he picked up the rest of the destroyed outfit, shoving them into the trash bag (he knew for a FACT Sammy couldn’t sew, no better than Jo and that said something) and was about to toss in the underwear but…  
Sam had clearly spent money on those, and it would just be a waste to throw them away. They were perfectly good underwear…  
Dean slipped the panties into his duffel bag after a moment of hesitation. He’d give them back to Sam, definitely, when he calmed down. Maybe he’d even get to see him wear-  
No. Fucking no, you are a grown ass man! Dean chastised himself, kicking the side of the bed frame. Sam, what the fuck Sammy? He was going to be the deathe of Dean.. What was he supposed to do now? How was he supposed to deal with that?  
He paced, distracted, until he stepped on something hard and heard a crunch. Oh shit.  
Sam’s CD player was officially broken, damage worse than before. Dean picked it up and opened it, hoping to see a safe CD. Instead he saw a cracked disc and sighed, closing it and placing it on Sam’s bed. It was about time to get him a new one anyways… Sammy loved that stupid CD.  
Fine. He’d go now, get a new disc player, and be back before Sammy noticed. The nearest Walmart was just down the road anyways.  
He grabbed his keys and slipped out the door. Hopefully Sammy would appreciate the gesture.  
****  
Sam sat on the edge of the tub, staring at his knees and trying not to start crying again. Dean had thrown a lamp, kicked something, broke something else, and left… He was not going to be okay. Sam felt numb, empty. Everything he’d ever fantasized about came back to him like a crushing wave of horror and dread. If Dean figured about this, it was only time until he learned the rest. Apparently Sam couldn’t keep a secret.  
He stood up, resolute, and began scrubbing his face. No makeup, no skirts, no dresses, Nothing but a sixteen-year-old heterosexual male from here on out. It didn’t matter what he thought he wanted. At least until he got to college. And that was that.  
After he was sure his face was washed clean, if a little shiny and red, he wrapped a towel round his waist and went out to grab some clothes. As he tossed his bag onto his bed, though, a plastic object caught his eye and he stopped breathing for a minute.  
Dean had broken his CD player. It sat there, an innocent piece of plastic and machinery, but Sam felt his chest practically collapse at the implications. He’d known Dean was mad but Dean had bought him that disc player with the money he’d scraped together a few years ago, and Sam treasured it. Had treasured it.  
A deep emptiness began to gnaw at his stomach and Sam pulled on a pair of pants, slipping into bed and deciding to feign sleep when Dean came back.  
***  
Dean stepped into the room quietly. The lights were out; Sammy was already asleep. Instead of waking him up, Dean determined to give the player to him when he next had a chance. Today had to have been stressful for him. He leaned over and patted Sam’s shoulder, then crawled into his own bed. It would all work out.  
****  
Except that he didn’t get to give Sam the disc player in the first week, and then it was too awkward. The next two months were cold on Sam’s side, increasingly desperate on Dean’s. He would try to communicate with Sammy in almost any way and get clipped, irritated answers. Dean knew it was because he’d thrown away the skirt, and he felt bad about that! But he had no idea how to fix it. (The increasingly frequent nights where he woke up imagining Sammy-only pornathons feat. Dress were NOT helping.)  
Until one day, right after they finished a hunt early and Dad decided to catch this one woman in white just a couple hours away, Dean you go home to Sam, and he figured it out.  
***  
Dean sped down the road in the Impala, thoughts on the night swirling round his mind. He patted the steering wheel and whistled absentmindedly. The hunt, pretty much by-the-books (which he was thankful for) had ended a whole day before he thought it was going to. He could head home, grab some take-out, and surprise Sammy with dinner and a movie. He still liked those, right? Dean hoped Sammy wouldn’t be too angry or angsty or whatever to accept Arby’s and The Wrath Of Khan. Even if they had both seen it a few times already, it was a classic. (Just in case though, Dean went by the local rental shop and borrowed a shitty old monster movie. Sam couldn’t reject a movie so awful, could he? Dean hoped not.) Plus, he had a surprise that required a quick stop at the mall.  
He turned into the Arby’s drive-thru and pulled in, looking to rattle off the name of the biggest, juiciest burger he could see. For Sam, though, he had to think. Was he still doing that vegetarian thing? Shit.  
“One roast beef with cheddar with extra meat and cheese… actually how about three of those, and… um…’ He scratched his slightly stubbly chin and considered his options for a moment. “And one big salad. No meat. But, uh, something that tastes good.” Dean finished lamely, looking at the blinking order screen for a moment before the girl answered through the light-up box. (What the fuck was that called anyways?)  
“So… a large salad and three melts? Anything else?”  
Dean grinned and ordered a couple drinks. Maybe getting him something Dad would never order would soften Sam up for tonight. Hopefully he would be up for what he had planned.  
He flirted with the girl at the window, grabbing his food and getting her number before heading home. He wasn’t going to use it, they’d be out of town by the weekend, but it was still a force of habit.  
The drive home was uneventful and Dean wondered what Sam was doing. Probably homework, like they weren’t going to be gone before the assignment was due. Hell, maybe he’d made a friend. He seemed big on those lately; friends that weren’t Dean. Dean frowned, then smirked. Hopefully he wouldn’t need those for long.  
As he pulled into the driveway he quieted the motor and coasted into a parking spot, opening the door quietly and sneaking over to their hotel’s door.  
****  
This time Sam had nothing to distract him. He’d been watching TV, laying on the bed in a pleated skirt and frilly top. (He’d told himself he would quit, but Dean didn’t talk to him about it, and he really missed the feel of fabric brushing around his legs freely.)  
“Dean!” Sam was shocked, tumbling off the bed, away from his brother in the doorway and landing on his ass on the floor, legs sprawled. He immediately pulled them together and prayed that Dean hadn’t seen his underwear, desperately searching for a reason he might have been wearing this. Something, anything to convince Dean he wasn’t seeing what he was seeing; that Sam had stopped. But nothing came to mind, and he felt his cheeks burning and himself tearing up as he watched Dean’s eyes slowly rake up and down Sam’s attire. Neither of them moved for a minute.  
“I…” He felt himself crumble, his throat closing up.  
Dean started at his voice, tearing his gaze away from Sam’s torso and to his face. He swallowed and Sam shrunk a bit more, wishing he could disappear.  
“I tried so hard Dean but it didn’t work because I couldn’t stop; they’re so pretty and nice and I don’t know, Dean, I’m so sorry-” Sam was rambling, terrified, and he could feel tears threatening to spill over his cheeks.  
“Please, please don’t hate me, please don’t tell Dad, I’m so sorry, I’ll just-” He began to take off the outfit, remembering the time this last happened. It wasn’t cooperating. Sam was about to just tear it to shreds when a heavy, warm came down on his shoulder and he completely froze, a broken sob escaping his throat.  
He couldn’t meet Dean’s eyes, but Dean reached out and nudged Sam’s chin up before he could flinch away.  
“Sammy.” The voice was even and smooth, didn’t sound angry, but Sam was shaking, could barely hear him over his own emotion.  
“Sammy. Look at me.” Dean said again, using a more commanding tone, and Sam looked up slowly.  
“Sam, Sammy, I am so sorry. Last time this happened, I reacted very badly.” Dean’s thumb reached up and wiped at Sam’s cheek, where a tear had escaped without his consent. “You are so pretty. I’m sorry for ever making you think otherwise. I, I was shocked, and I’m sorry. Sammy!”  
Sam was looking away, trying to tug his arms out of Dean’s grip. “Stop it, Dean, I don’t need your pity, let me go, let me-”  
He was stopped with a kiss. All at once the fight went out of him and he froze, letting himself do nothing but feel Dean’s lips on his. What was going on?  
***  
Dean pulled away after he was sure Sammy wouldn’t try and bolt. He brushed the hair out of Sam’s eyes and smiled at him.  
“You’re really pretty, you know that? I like this on you.” He gestured to the outfit, disheveled from where Sam tried to pull it off. “I was freaked out at first, but you were so pretty in that outfit the first night, I had dreams about it.”  
Sam, Sammy, looked up at him, confused. “But, but you… You broke my CD player!” He reminded Dean. “You threw things! You left me.” His voice cracked on the last one and he looked away.  
It was Dean’s turn to look confused. “I, but I… Oh shit.” Dean took Sam into his arms and hugged him tight. “I’m so sorry… For all those things. I did throw something, but your CD player was an accident. I left to… to get you a new one. I felt bad, and wanted to tell you you looked great, but I couldn’t. I mean,” He pulled away and took Sam’s face in his hands, “How could I tell you that, the way I wanted to, when we’re brothers?”  
Sam looked up at him, lower lip quivering, and sniffed. “You mean you’re not mad?”  
“I’m anything but mad. You’re gorgeous.” Dean smiled down at him. “And I know I’m going to Hell for this, but you’re so beautiful Sammy, and I want to kiss you. God, you’re stunning. Is that okay?”  
****  
Sam slowly nodded. This was what he had wanted, and he was somehow getting it. He hoped it wasn’t a dream.  
Dean pulled him in, more slowly this time, and kissed him softly. Sam sighed into it, and melted. His brother’s lips were soft and warm, a little damp from his licking habit, and it was perfect. They slotted together like two pieces of a puzzle and it was all too soon when Dean pulled away.  
Sam tried to follow him with his lips but Dean laughed and nudged his chin away with his fingers.  
“I brought dinner and a movie… and a present for you. Two, I guess.” Sam watched as Dean stood and grabbed something out of his bag, eyes widening when he saw the item.  
It was a new CD player, much better than the cheap old one Sammy had been using before it’d been… damaged. Sam grabbed it from Dean’s extended hand, looked it over for a second, then tossed it on the bed and flung himself at Dean.  
“Thank you, thank you!” He felt like giggling. Dean wasn’t mad at him, didn’t hate him, thought he was pretty? It was wonderful.  
“I also…” Dean pulled away slowly and Sam let him, watching him dip into his bag and pull out… Oh my god.  
Dean pulled out a gorgeous red skirt, holding it out for Sam to take.  
Sam hesitated, staring at it.  
“Why did you…” He trailed off.  
“I want to see you in it. I want to see how beautiful you look. Please Sammy?” He smiled and Sam wanted to. For Dean, he wanted to show off the skirt.  
He grabbed it and disappeared into the bathroom, the irony of the situation not lost to him. Last time he’d run to the bathroom there was a very different reason. He pulled the skirt off and put on the one Dean had held out for him, thankful the blouse he’d been wearing was white. No need to worry about matching.  
He left the room slowly, peeking out and seeing Dean smile encouragingly.  
Sam stepped out and heard an audible intake of breath. He looked away shyly, then glanced up from under his lashes to see Dean staring at him, mouth slack and face red.  
“Wow… Sammy… You look so beautiful.” Dean shook his head and a huge grin split his face. “Spin for me, Baby?” he paused, looking slightly embarrassed for his slip-up, but Sam blushed bright red and smiled, nodding slowly and turning so Dean could see all of him.  
When he faced Dean again, he noticed Dean was breathing funny. A quick glance at Dean’s pants told him why, and he felt like passing out. Dean was… what?  
“Sammy, you are so pretty, so wonderful, beautiful… Come here.” Dean gestured him forward and Sam walked over to him, his own arousal making itself known at the front of his skirt.  
Dean pulled him into an embrace and kissed him, harder than before, and reached down to rub Sam’s ass through the fabric. Sammy whined through the kiss and allowed Dean into his mouth, deepening the kiss.  
Sam felt warm, comfortable. Dean accepted him. Even though it’d taken a whole lot of misunderstanding, he was okay with Sam’s clothing. Not only that, he thought he was pretty.  
“Dean… How pretty am I?” He asked, pulling away a little.  
Dean smiled at him, rubbing Sam’s cheek with his thumb. “You’re the prettiest person I’ve ever seen.”  
Sam ducked his head and kissed Dean lightly on the cheek.  
“Do you love me?”  
Dean didn’t even hesitate. “I love you so much, Sammy… So goddamn much.”  
Sam felt like his heart would burst. “I love you too, Dean."


End file.
